Leonard asked where the adjective plug-ugly came from. It has come to mean unspeakably ugly in the physical sense.
The original Plug Uglies were street thugs in Baltimore, Maryland, in the mid-nineteenth century. They acted as enforcers for politicians who wanted to control elections, and as musclemen for private enterprises such as competing fire companies, which were freelance, profit-driven, and fiercely cutthroat in those days.
The plug portion is explained by a couple of theories. One of them, noting that the gang worked for the Mount Vernon Hook & Ladder Company, ties it to fireplugs, a word that showed up in 1707. The other notes that the distinctive gang headgear—protective stovepipe hats—were called plugs beginning in 1848.
Ugly, I think it is safe to say, did not originally refer to the physical appearance of gang members. Ugly has been used to refer to offensive, repulsive, and immoral behavior since 1300. The Plug-Uglies may have taken pride in being thugs and hooligans, but their behavior was ugly to decent Americans.
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